Triethyloxonium tetrafluoroborate → HCID 21495341, compound

HRID 1731140Notes

Reaction equation

HRID 1731140 reaction equation
F[B-](F)(F)F.C([O+](CC)CC)C.[CH3:13][NH:14][C:15](=O)[CH2:16][CH2:17][C:18]1([CH3:31])[C:23]2[CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=3[C:22]=2[CH2:21][CH2:20][O:19]1>C(Cl)Cl>[CH3:13][NH:14][CH2:15][CH2:16][CH2:17][C:18]1([CH3:31])[C:23]2[CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=3[C:22]=2[CH2:21][CH2:20][O:19]1

Participants

4

Reactant 2

HCID 2723982Triethyloxonium tetrafluoroborateHCID 21495275HCID 21495275, compound

Product 1

HCID 21495341HCID 21495341, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of triethyloxonium fluoroborate (3.5 g) and the amide of formula X, N,1-dimethyl-1,3,4,9-tetrahydroindeno[2,1-c]pyran-1-propionamide (5.5 g), described in Example 108, in 100 ml of methylene chloride is evaporated at reduced pressure and the residue dissolved in 50 ml of absolute ethanol. Sodium borohydride (1.35 g) is added in portions to the stirred solution at 0° C. When the addition is complete, stirring is continued for 18 hr. at 25° C. The solution is poured into 250 ml of water and extracted with 3 × 30 ml portions of ether. The combined extracts are washed with water, dried (MgSO4) and evaporated yielding the title compound, identical to the product of Example 285.

Workup

  1. customis evaporated at reduced pressure
  2. dissolutionthe residue dissolved in 50 ml of absolute ethanol
  3. additionSodium borohydride (1.35 g) is added in portions to the stirred solution at 0° C
  4. additionWhen the addition
  5. customat 25° C
  6. additionThe solution is poured into 250 ml of water
  7. extractionextracted with 3 × 30 ml portions of ether
  8. washThe combined extracts are washed with water
  9. dry with materialdried (MgSO4)
  10. customevaporated

Sources & evidence

ORD record
ord-5042efa4ccc6488a8422fc4bf2e32da5
Source dataset
uspto-grants-1976_11
Patent number
US03995052

Reaction notes

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